Daring Dabbs

The following story is fiction and does not describe any real person or situation in particular. All characters are at least eighteen. This is a story about a man who tries to deal with his inappropriate desires and a young woman who wants to give him what he needs. The plot has elements of several categories, but the main one is "reluctance" so I placed it here. Remember, the story is FICTION and just a FANTASY so just have fun reading. -- xoxo Daphne

*****

Never in my many years of teaching did I expect to have a student quite like Deborah (she went by 'Dabbs' for short). She came through the school during the early part of my career as a high school history teacher, and over the years I saw her grow up from a cute girl into a beautiful young lady.

Dabbs was always a good student. She loved history and was very attentive in class. She was also a lot of fun. Spontaneous, flirty, and a bit of a thrill seeker, you never knew quite what to expect from her.

Dabbs had gorgeous blue-gray eyes, long light brown hair, and a slightly naughty smile. She was never shy, and always spoke her mind in the most matter-of-fact way possible. Her voice was very cute, authoritative, sometimes sassy, and she had a slight southern accent that was incredibly endearing.

After Dabbs graduated, she fell off my radar for a while. In fact, it was her that made contact again many years later. Now in her mid-20s, Dabbs had gotten her education degree and was teaching at a nearby high school. Over the span of the next several months, we met for lunch or coffee and got to know each other really well as adults. We talked about everything from family and career to philosophy and experiences.

To be more specific, sexual experiences.

Apparently, Dabbs had been rather physical in high school, something I suspected at the time but didn't know for sure. She was always careful and safe, but had a very open mind about having sexual experiences and didn't have any issues with casual hookups.

It felt surreal to hear a former student of mine candidly tell me about the time she fucked discretely in a dark movie theatre, and describe various encounters in the back seats of cars. She admitted she loved being spanked, giving blowjobs, and being lightly choked while fucking.

What really grabbed my attention though, was when she admitted to having a thing for older men. She wasn't flirting with me at the time...at least I didn't think so. She was just nonchalantly mentioning a particular kink of hers.

What Dabbs didn't know, was that I had been fantasizing about fucking her for months now, and I was feeling guilty about it.

Really guilty.

First, as a former student, I had known Dabbs since she was 14 years old. It just didn't seem right to be lusting after someone I used to teach, even now that she was all grown up and in the same profession as me.

What seemed even more inappropriate, however, was the age gap. At 24, Dabbs was literally half my age. I tried very hard to think of her as a student who was off limits, but all I could picture in my mind was Dabbs on her knees looking up at me with her beautiful eyes as she sucked my cock dry. I felt so ashamed for having these thoughts and promised myself I would never act on them.

So, as I've done pretty much most of my life, I became the "sweet friend" of a gorgeous girl who fucked other people.

As both of us were teachers, Dabbs and I would travel in the summer as friends and had some wonderful trips together. England, France, Austria, we had a marvelous time everywhere we went, seeing new places and trying new things.

It was when we were in Germany, however, where things between Dabbs and I got a bit more...complicated.

We were enjoying a wonderful day in one of Munich's outdoor beer gardens, just talking and having what Germans call "ein mass" (essentially a liter of beer in a clear mug). Dabbs was very capable of downing several liters and only getting a little tipsy. After one or two though, her inhibitions lowered, and she began to talk about things we wouldn't normally discuss.

Unlike Dabbs, my tolerance for German beer was pretty low, so I began to admit things I'd normally never tell anyone.

...and it all started with a question.

"Do you not like your drink?" Dabbs asked, noticing I had only emptied about half of my mug as she was finishing her second liter.

"Oh, it's fine," I replied, "I just don't want to have too much."

Dabbs looked at me thoughtfully for a moment. "You're always so reserved and sensible. Have you never let yourself lose control before?"

"Not really," I shrugged.

"Never been smashed?" Dabbs pressed her question. "Never partied all night? Never had a wild sexual experience?"

"I've had sex before," I insisted.

"I imagine it would have been pretty vanilla, though," Dabbs wondered out loud.

"You'd be surprised," I said without thinking.

"Really?" Dabbs raised her eyebrows. "Like what?"

"You know, dirty talk, spanking, some handcuffs, some role playing."

"Well, okay then, I'm impressed," Dabbs took another sip of her drink.

"Well, it's not like doing it in a movie theatre," I countered.

My former student cocked her head to one side and smiled slyly. "So when was the last time you fucked someone?"

I thought for a moment. "About fifteen years ago."

Dabbs almost choked on her drink. "What!?!?"

Only after I said it did I realize how pathetic that made me sound.

"Are you serious? Why so long?" Dabbs asked, still a little taken back. "Lack of interest?"

"No," I replied, "more a lack of opportunity. It takes two people you know."

Dabbs smiled naughtily. "Sometimes three..."

I gave a slight laugh.

"Do you at least jerk off to get some relief?" Dabbs asked so casually that it caught me off guard.

"Oh sure," I replied.

"Well, that's good at least."

...and then...without thinking...I said it.

"Sometimes while I'm looking at your picture."

Dabbs eyes went wide in surprise, and she smiled.

"Really? Wow, I'm flattered," she almost seemed excited. "How long have you fantasized about me?"

I felt ashamed for admitting it. "For a while now, ever since you came back into my life."

Dabbs took my hand gently. "Why didn't you tell me?"

I started to well up. "It felt wrong to fantasize about you."

"Does is bother you that I used to be one of your students?"

"Actually, it's kinda hot," I answered, "and that's the problem. The idea really turned me on, and it made me feel unbelievably guilty about having those thoughts about you."

"So it's like the 'forbidden fruit' thing?" Dabbs asked as if she were a therapist talking to a patient.

"Yeah, I guess so," I said, really hoping I hadn't damaged our friendship by admitting to all this.

After an awkward silence that seemed to last forever, Dabbs looked directly at me with the most serious expression I'd ever seen her give anyone.

"Do you still want to fuck me?"

I probably shouldn't have said it, but Dabbs was someone I just couldn't lie to either.

"Yes," I confessed.

"Well okay then," Dabbs said matter-of-factly. "So, do you want to go to the hotel room?"

I blinked a few times, taking in what she had just said. Was she really going to go through with it?

"I...can't, Dabbs," I said experiencing the most torturous internal conflict of my life. "I want to, so badly, but it just isn't appropriate. You're a former student...I just can't."

"Are you worried about someone finding out?" Dabbs asked. "We're half a world away, no one would know if we went back to the hotel room and I sucked your dick."

I was so embarrassed when I noticed that Dabbs could see my rock hard cock through my trousers.

"I would know," I admitted, "and I couldn't live with myself."

Dabbs rolled her eyes in frustration.

"What I really need is for you to rape me so I don't have a choice," I said only half-joking.

Dabbs gave a slight laugh. "You're funny."

"Yeah," I replied with unbelievable sarcasm. "I'm freakin' hilarious."

My former student looked at me sympathetically. She could see how conflicted I was, and how much guilt I was experiencing.

"Come on," she said standing from the table, "let's go for a walk."

Dabbs and I spent the next few hours walking around Munich's English Garden and sightseeing, pretty much conversing about everything except what we really needed to talk about...my guilt-ridden desire to fuck her, and her willingness to let me do it.

We had a wonderful dinner that evening with some amazing Bavarian beer. Dabbs playfully made sure I finished my liter and then ordered a second one.

"Oh come on, live a little," Dabbs urged, "you can go to bed after dinner and sleep it off."

Afterwards, we walked back to the hotel together. Dabbs said good night to me in the lobby, giving me a sweet kiss on the cheek as I headed to my room.

I was so tired that I didn't even bother to change clothes, I just curled up on top of the bed and drifted off to sleep. The German beer made me sleep really deep as well...so much so that when I woke up in the middle of the night, I didn't immediately realize that I wasn't on my bed anymore.

"Wha- what the..." I stammered as my head began to clear a little. It was pitch black in the room, and I wasn't where I was supposed to be.

The first thing I noticed was that I was sitting on a chair, one of the cushioned desk chairs from the hotel room.

The second thing I noticed was that I was tied to it.

My wrists were restrained behind my back and my ankles were tied to the chair legs.

"What the..." I began pulling on the restraints, trying to break free.

(click)

I heard the lock of a door...

I wasn't alone...

"Dabbs?" I whispered hesitantly. "Dabbs, is that you?"

"Mmm hmm," I heard her cute voice in the darkness. "It's me."

"What the heck is going on?"

The lights came up a little, and I saw Dabbs in front of the connecting door to our rooms with her hand on the dimmer switch.

When the room had enough light for me to see Dabbs clearly, my heart nearly stopped.

Dabbs, my student from ten years ago, a girl half my age, now a friend and professional colleague, stood on the other side of my room. Around her waist was the cutest little pink pleated skirt with a plaid design, it's length just barely covering the top of her legs. Her large breasts were braless and straining against a tight-fitting, white, button-down shirt, while a pair of soft pink ankle boots with two-inch heels gave her a little extra height. Her long light brown hair was hanging down to her shoulders and pinned up into pigtails with little pink bows that matched her ankle boots and short skirt.

I sat there gaping at my former student as she turned her body sideways and raised her left leg in a flamingo pose, modeling her outfit and smiling cutely as if to say, "look at how adorable I am."

I swallowed hard, and tried to make words come out of my mouth.

"D—Dabbs," I said uneasily, "what do you think you're doing?"

Without answering my question, Dabbs got down on all fours and slowly began to crawl towards me, her beautiful eyes locked on mine.

"Dabbs?" My voice was more shaky this time.

She didn't answer...

I could see Dabbs' wonderfully round ass in the reflection of the full length mirror attached to the wall as she crawled on all fours towards me, something she had obviously planned to drive me insane. Her little schoolgirl skirt was riding up as she crawled, revealing the white thong panties she was wearing underneath her skirt, and giving me an unbelievable view of her practically bare and perfectly round ass.

"Dabbs..." I was starting to get really afraid, "...this is wrong. Please, this is so wrong."

Dabbs' beautiful bright eyes were filled with purpose. She wasn't going to stop. She KNEW that I still saw her as my student. She KNEW I had fantasized about her. She KNEW I was racked with guilt for having thoughts of fucking a girl I used to teach.

Worst of all, she knew she could use that against me.

Dabbs was totally aware of what I really wanted, but wouldn't admit to myself. I wanted to actually fuck my student. So, the 24-year-old Dabbs decided to become my 18-year-old student once again...and make her unbelievably hot by doing the things that turned me on the most.

As Dabbs reached the chair to which I was restrained, she placed both her hands on my knees and, in one quick motion, spread them apart.

"Um!" I grunted as my legs were forced open.

Dabbs kept her eyes locked on mine as she began unbuttoning my trousers and pulling down the zipper.

"Mygod, Dabbs!" I panicked. "Please don't, this isn't right! This isn't..."

I stopped mid-sentence when I felt my former student tug my boxers down and grasp hold of my unbelievably hard cock.

"Mmm hmm...I thought so." Dabbs finally spoke, flashing a naughty look at me as she began pumping my shaft in long slow strokes.

"Ohhhh," I laid my head back and closed my eyes. It had been years since someone else had touched my cock, and it was absolutely throbbing with the need for attention.

"Don't close your eyes," Dabbs instructed, "look at me."

I stared at the ceiling and shook my head, unable to make eye contact with a girl half my age who used to be a student and now had my hard throbbing cock in her hand.

Oh, why was she doing this to me?

Continuing to tease my shaft with long, slow pumps, Dabbs began giving the head of my cock little licks and sucks and kisses as she spoke with authority.

"You might as well look at me...(kiss)...because I'm not stopping...(suck)...we both know that you want me...(lick)...you WANT to fuck your student don't you?...(kiss)."

"Dabbs...please..." I begged shamelessly. "It's wrong."

Dabbs giggled.

"That's what makes it sooooo hot...(lick)...the fact that you used to teach me...(suck)...that I was off limits to you...(kiss)...the more you thought you couldn't have me...(suck)...the more you wanted my pussy...(lick)."

"Ohgod..." I whimpered.

"This cock wants to be inside me...(suck)...it's harder than any cock I've ever seen before...(lick)...so now's your chance...(kiss)...you can use it to fuck my face...(lick)...you can stick it inside my pussy...(kiss)...I'll let you do anything you want to me..."

"Ohgod...no please..." My world came crashing down as I felt Dabbs slowly envelop the entire length of my cock. The sensation of my student's warm moist mouth completely surrounding my member was unlike anything I'd ever felt before. The girl to whom I used to give homework assignments every day was now sucking on my dick, and it felt amazing.

As Dabbs began bobbing her head back and forth, she moaned in pleasure as if giving blowjobs was her favorite thing in the world to do...maybe it was. She certainly knew what she was doing. Her tongue swirled around the head of my cock, hitting my most sensitive spots each time she took the full length of my shaft into her warm wet mouth. The suction on each retracting pull was unbelievable, Dabbs making wonderfully loud slurping noises as she expertly worked every inch of my pleasure stick.

I had to look.

When I glanced down, I saw Dabbs on her knees, her head bobbing, her schoolgirl pigtails swishing back and forth, and her gorgeous eyes looking up at me.

"Oh fuck, Dabbs," I whimpered shamelessly. "Ohgod, what are you doing to me?"

In response, my former student gave my shaft a long hard pull with a suction so intense it made me cry out.

"Ohgod!" I yanked on my restraints in tension, unable to escape her torturous mouth.

Dabbs giggled at the pleasure sounds she was pulling out of me...and it just encouraged her more.

Faster and faster Dabbs went down on my cock. Every torturous head bob, every tickling swish of her pigtails, every flutter of her beautiful eyes, made me feel the most amazing guilt and wonderful bliss at the same time.

"OH!" I gasped in an overload of pleasure as Dabbs sucked off my cock from the base to the head in one massive pull. It felt like every nerve in my body was being forced through my shaft and preparing to explode from my tip. With amazing suction, my student's warm wet mouth gripped my over sensitive head from all directions and pulled off slowly, finally releasing my member, leaving it throbbing and desperate for more attention. As I gasped for air, Dabbs tilted her head to one side and smiled naughtily.

"Admit it," she said, continuing to jerk off my cock with her hand as she talked. "You've always wanted to have a student sucking your dick. I'm driving you fucking crazy right now in this little schoolgirl outfit...and you can't stand it."

Dabbs gave the head of my cock a teasing lick, causing me to shiver. Her amazing sucking skills had made my cock so sensitive. As if that wasn't enough torture, Dabbs then placed her thumb at the very tip of my member and began rubbing steadily in tiny little circles.

"Oh!!" I gasped as bolts of pleasure shot through me with every circular stroke.

"You want to fuck your student, don't you?" Dabbs taunted.

My eyes welled up.

"You want me to suck your dick dry."

I clinched my jaw in tension.

"Well get ready you little perv," Dabbs gave me a dangerous look, "because here it comes."

In one motion, my student took the entire length of my cock into her mouth, practically swallowing my entire shaft.

"OH FUCK!" I cried out as I felt the tip of my cock hit the back of my student's throat and she began to suck violently.

(gluh gluh gluh gluh)

Dabbs half-choked and half-swallowed as she deep throated my large member, her pigtails caressing my inner thighs, and her blue-gray eyes looking up into mine.

(gluh gluh gluh gluh)

"OHGOD DABBS!!" I pleaded shamelessly. "THIS IS TORTURE!!"

The look my former student gave me as she expertly deep-throated my cock was one of pure submission, as if she had forgotten her homework and was trying to convince me not to tell her parents. It was such a good act, and played into my most taboo fantasies. Dabbs knew EXACTLY what she was doing to me, and had no intention of stopping.

(gluh gluh gluh gluh)

"OH!!" I gasped as Dabbs began bobbing at full speed, her pigtails swishing wildly as her submissive stare became one of determination and purpose.

"FUCK! OH FUCK!!" I cried out, "DABBS!! PLEASE STOP!!"

"Mmm mmm," my former student shook her head, not even letting up for a moment.

"OH FUCK!! FUCK!! FUCK!!" I could feel the climax approaching, the wet slurping sounds getting louder and louder. My student was going to pull the orgasm out of me whether I wanted it or not.

Out of the corner of my eye, I could see the surreal image in the wall mirror's reflection. I saw myself being sucked off by my former student who was on her knees, dressed as an 18-year old schoolgirl. I could see her short skirt hiked up over her hips, showing the thong panties that were riding up her large round ass. I could see the back of her head bobbing on my shaft as she made the most obscene sucking and slurping noises. I could see her pigtails hitting against my inner thighs as she tortured my cock relentlessly. I could see her hands on my knees, holding my legs apart as she went down on me, completely ignoring my pleas to end the torture.

Without showing any signs of mercy, the schoolgirl sucked and sucked and sucked.

"No! No Dabbs!! NO!! DON'T!!" I begged as we both felt my cock get larger inside her hot wet mouth.

"MMM!!" Dabbs' eyes widened as my cock exploded.

"OHHHHH!! FUUUUCKK!!" I tossed my head back as I fired down my student's throat, her suction continuing to relentlessly torture my pulsating member.

As Dabbs took everything my cock gave her, my body began trembling and convulsing from the pleasure overload. Dabbs watched as she continued her unbelievable suction, pulling everything out of me.